WO2016004867A1 - Process for producing aromatic primary diamines - Google Patents

Process for producing aromatic primary diamines Download PDF

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Publication number
WO2016004867A1
WO2016004867A1 PCT/CN2015/083535 CN2015083535W WO2016004867A1 WO 2016004867 A1 WO2016004867 A1 WO 2016004867A1 CN 2015083535 W CN2015083535 W CN 2015083535W WO 2016004867 A1 WO2016004867 A1 WO 2016004867A1
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WO
WIPO (PCT)
Prior art keywords
amine
reaction
ammonia
aromatic
aromatic dialdehyde
Prior art date
Application number
PCT/CN2015/083535
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English (en)
French (fr)
Inventor
Peng Li
Floryan Decampo
Original Assignee
Rhodia Operations
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Rhodia Operations filed Critical Rhodia Operations
Priority to CN201580037775.9A priority Critical patent/CN106488905B/zh
Priority to CN201911137833.1A priority patent/CN111116528B/zh
Priority to BR112017000203-5A priority patent/BR112017000203B1/pt
Priority to EP15819072.8A priority patent/EP3166921B1/en
Priority to EP20157956.2A priority patent/EP3674285B1/en
Priority to KR1020177002283A priority patent/KR20170027792A/ko
Priority to US15/324,932 priority patent/US10899726B2/en
Priority to JP2017500926A priority patent/JP6704896B2/ja
Publication of WO2016004867A1 publication Critical patent/WO2016004867A1/en
Priority to US16/781,356 priority patent/US11066377B2/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
    • C07C209/26—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with hydrogen
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J25/00—Catalysts of the Raney type
    • B01J25/02—Raney nickel
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical

Definitions

  • the present invention relates to a process for producing aromatic primary diamines by reductive amination of their corresponding aromatic dialdehydes.
  • US 2636051 A (SHELL DEV) 4/21/1953 discloses a process for preparing long-chain aliphatic primary diamines upon conversion of aliphatic dialdehydes wherein the formyl groups are separated by at least four carbon atoms, by feeding the aliphatic dialdehyde to a reactor containing ammonia, hydrogen and a hydrogenation catalyst at a controlled flow rate, and provided an example with 60%yield of the primary diamine product using a Raney nickel catalyst and water solvent.
  • organic solvents include: alcoholic solvents such as methanol or ethanol; aromatic hydrocarbon such as toluene; and ether solvents such as tetrahydrofuran, 1, 4-dioxane, and methyl-t-butyl ether.
  • alcoholic solvents such as methanol or ethanol
  • aromatic hydrocarbon such as toluene
  • ether solvents such as tetrahydrofuran, 1, 4-dioxane, and methyl-t-butyl ether.
  • US 6696609 KURARAY CO.
  • LTD 4/3/2003 suggested the preference on methanol or ethanol, and emphasized that the proportion of primary amine in the reaction mixture should be minimized, in order to produce the desired aliphatic diamines (i.e. 1, 9- nonanediamine and 2-methyl-1, 8-octanediamine) with a high yield of above 90%.
  • desired aliphatic diamines i.e. 1, 9- nonanediamine and 2-methyl-1, 8-octanediamine
  • this object is achieved by the present invention using a new process to prepare aromatic primary diamine by reductive amination of its corresponding dialdehyde, which does not diminish amine presence in the reaction mixture but rather keeps a minimal amine/dialdehyde ratio at the start of the reaction, in order to increase the product yield.
  • the present invention provides a process for the production of an aromatic primary amine, the process comprising reacting an aromatic dialdehyde with hydrogen and ammonia or an ammonia-liberating compound, in the presence of a hydrogenation catalyst and an amine, wherein the molar ratio of the amine to the aromatic dialdehyde is no less than 1: 4 at the start of the reaction.
  • aromatic primary diamine can be produced in high yields and at an economical cost.
  • This effect which is a new finding of the present inventors, is contrary to the prior art teaching on the suppression of primary amine in the reaction mixture to favour the intended reductive amination.
  • the present process can be readily adapted for batch or continuous operation mode, thus applicable to a wide range of industrial applications.
  • amine refers to an organic compound derived by replacing one or more of the hydrogen atoms in ammonia by an organic group, and includes primary, secondary and tertiary amines.
  • the amine used at the start of the reaction in the present process is a primary amine or a secondary amine, more preferably a primary amine.
  • a “primary amine” is a compound of the formula RNH 2
  • a “secondary amine” is a compound of the formula HNRR’
  • a “tertiary amine” is a compound of the formula NRR’R”, wherein R, R', R” are each independently an organic radical.
  • aromatic primary amine refers to an aromatic compound which is also a primary amine.
  • R, R' and R may be independently selected from the group consisting of alkyl, cycloalkyl, aryl, heterocyclyl, heteroaryl, alkylcycloalkyl, alkylaryl, alkylheterocyclyl, alkylheteroaryl, and alkoxyalkyl.
  • R, R' and R” are independently selected from a group consisting of straight or branched (C1-C10) alkyl, phenyl (C1-C3) alkyl, and heteroaryl (C1-C3) alkyl, each optionally substituted with substituents selected from the group consisting of halogen, hydroxy, alkoxy, amino, nitro, halogen, cycloalkyl, and alkyl.
  • the amine used at the start of the reaction is a primary amine.
  • primary amines used at the start of the reaction of the present process include methylamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine, benzylamine, cyclohexylamine, ethylene diamine and the like.
  • Preferred primary amine examples notably include methylamine, butylamine, pentylamine, and hexylamine, of which methylamine and butylamine are further preferred.
  • butylamine generally gives a vapour pressure high enough at low temperatures in the reaction system, thus permits easy recovery.
  • aromatic diamines obtainable from the present process are also usable as the amine ingredient at the start of the reaction.
  • the amine used at the start of the reaction in the present process is a secondary amine of the formula HNRR’, wherein R and R' are as defined above.
  • the amine used at the start of the reaction in the present process is a tertiary amine of the formula NRR'R”, wherein R, R' and R” are as defined above.
  • Exemplified secondary amines used at the start of the reaction of the present process include dimethylamine, diethylamine, diethanolamine, dicyclohexylamine, diallylamine, piperidine, pyrolidine, morpholine, N-methylbenzylamine, dibenzylamine and the like.
  • Preferred secondary amines used in the present invention include dimethylamine, diethylamine, and N-methylbenzylamine.
  • Exemplified tertiary amines used in the reaction of the present process include trimethylamine, triethylamine, triethanolamine, diisopropylethylamine, tricyclohexylamine, triallylamine, benzyldimethylamine, N-methylmorpholine, N-methyldibenzylamine and the like.
  • Preferred tertiary amines used in the present invention include trimethylamine, triethylamine, and benzyldimethylamine.
  • aromatic dialdehyde refers to a compound having at least one aromatic ring substituted with two aldehyde groups.
  • the aromatic ring as used herein can be a hydrocarbon or heterocyclic ring, and may be selected from a group consisting of benzene, pyrene, furan, thiophene, terthiophene, pyrrole, pyridine, terpyridine, pyridine oxide, pyrazine, indole, quinoline, purine, quinazoline, bipyridine, phenanthroline, naphthalene, tetralin, biphenyl, cyclohexylbenzene, indan, anthracene, phenanthrene, fluorene, and azulene, each being optionally substituted with at least one substitution selected from a group consisting of C 1 -C 24 alkyl, amino, hydroxyl, carboxyl, ester, cyano,
  • aromatic dialdehyde used in the invention include those having at least one furan ring substituted with two aldehyde groups, such as 2, 5-diformylfuran (DFF) and its derivatives.
  • DFF 2, 5-diformylfuran
  • aromatic dialdehydes are known in the art and can be readily prepared by, for example, hydrolysis of dihalides, Gattermanns carbon monoxide synthesis using formyl chloride or the equivalent thereof, and oxidation of various aromatic materials.
  • the present process requires that, at the start of the amination reaction, the molar ratio of the amine to the aromatic dialdehyde is no less than 1: 4, preferably no less than 1: 2, and more preferably no less than 1: 1.
  • the molar ratio of the amine to the aromatic dialdehyde is no more than 4: 1, preferably no more than 3: 1, and more preferably no more than 2: 1.
  • the molar ratio of the amine to the aromatic dialdehyde may be then comprised between 1: 4 and 4: 1, more preferably comprised between 1: 2 and 4: 1 (limit inclusive) .
  • ammonia or an ammonia-liberating compound or mixtures thereof may be used.
  • ammonia-liberating compounds include urea, uric acid, ammonium salts and derivatives of a primary amide, for example, symmetrical and unsymmetrical carbamates, carbaminates, semicarbazides and semicarbazoles, or aminium salts or organic/inorganic esters thereof.
  • Preference may be given to using ammonia itself, with liquid or gaseous ammonia being able to be used in this embodiment.
  • a value in the range of 1: 2-1: 50 and preferably in the range of 1: 5-1: 20 may be set.
  • the hydrogenation catalyst usable for the present process may be selected from Raney catalysts such as Raney nickel, Raney cobalt and Raney copper.
  • said hydrogenation catalyst may be selected from supported catalysts comprising a metal having hydrogenation activity such as nickel, cobalt, platinum, palladium, rhodium, ruthenium or copper on a support such as Kieselguhr, silica, alumina, silica-alumina, clay, titania, zirconia, magnesia, calcia, lanthanum oxide, niobium oxide or carbon.
  • These hydrogenation catalysts may have any shape such as powder, grains or pellets.
  • the amount of the hydrogenation catalyst used may vary according to the desired reaction rate, and it is desirably in a range of 0.01 to 30%by weight based on the weight of the reaction mixture, more preferably in a range of 0.1 to 10%by weight on the same basis.
  • the hydrogenation catalyst may be used in the form of suspension or as a fixed bed.
  • Nickel hydrogenation catalysts include those commercially available under the trade designations “PRICAT 9908” , “PRICAT 9910” , “PRICAT 9920” , “PRICAT 9932” , “PRICAT 9936, ” “PRICAT 9939” , “PRICAT 9953” , “PRICAT 20/15 D” , “PRICAT NI 52/35” , “PRICAT NI 52/35 P” , “PRICAT NI 55/5 P” , “PRICAT NI 60/15 P” , “PRICAT NI 62/15 P” , “PRICAT NI 52/35 T” , “PRICAT NI 55/5 T” and “PRICAT NI 60/15 T” (available from Johnson Matthey Catalysts, Ward Hill, Mass.
  • Hydrogenation catalyst may also be chosen from nickel catalysts such as Ni/PrO2-CeO2 catalysts and CuNiOx catalysts, optionally comprising another metal such as Zn or Pd for instance.
  • the amination reaction of the present process is desirably carried out under a hydrogen partial pressure in a range of 0.1 to 25 MPa, and more preferably in a range of 0.5 to 20 MPa.
  • hydrogen may be added during the reaction to make up for the consumption or continuously circulated through the reaction zone.
  • the amination reaction of the present process is carried out in a liquid phase using a solvent.
  • the solvent used should be liquid under the temperature and pressure throughout the amination reaction, and substantially inert to the reactants and products in the reaction mixture of the present process.
  • Suitable examples of such solvent include: alcoholic solvent such as methanol, ethanol, 2-propanol, 1-butanol, isoamyl alcohol and n-octyl alcohol; an aromatic hydrocarbon solvent such as toluene; or an ether solvent such as methyl t-butyl ether, tetrahydrofuran and 1, 4-dioxane, among which methanol and ethanol are preferred.
  • solvents may be used in any amountwith no specific restrictions, but desirably in an amount ranging from 0.5 to 50 times the weight of the aromatic dialdehyde used, and more preferably in an amount of2 to 10 times the weight of the aromatic dialdehyde used.
  • the reaction temperature is desirably in a range of 40 to 200°C, more preferably in a range of 100 to 150°C.
  • the reaction can be carried out either batchwise or continuously. In either case, it is recommended to feed the aromatic dialdehyde in a manner to ensure that the molar ratio of amine to the aromatic dialdehyde is no less than 1: 4 throughout the reaction, and is preferably in a range of 1: 4 to 2: 1, more preferably in a range of 1: 1 to 2: 1.
  • Suitable reaction vessels for carrying out the amination reaction of the present process may be selected from conventional types of autoclaves and conventional types of tubular reactors.
  • the reactor may be operated under the atmospheric pressure or under a partial pressure of 0.1-20 MPa, preferably 0.5-10 MPa and more preferably 1-3 MPa.
  • This pressure may be generated by injected hydrogen and ammonia and/or by pressurization of the reactor with a further, preferably inert gas such as nitrogen or argon and/or by formation of ammonia in situ from an ammonia-liberating compound or mixtures thereof and/or by setting of the desired reaction temperature.
  • the sequence of adding different reactants is not strictly limited.
  • an aromatic dialdehyde or its solution in a solvent is fed together with ammonia to a reaction vessel filled with a hydrogenation catalyst, amine, asolvent and hydrogen.
  • hydrogen was introduced in a reaction vessel containing a premix of an aromatic dialdehyde, amine, ammonia and a hydrogenation catalyst in a solvent.
  • the aromatic dialdehyde is dropwise added to a reaction vessel containing a premix of an amine, ammonia, hydrogen and hydrogenation catalyst in a solvent.
  • the amination reaction of the present process gives an aromatic diamine corresponding to the dialdehyde used, e.g. 2, 5-bis (aminomethyl) furan (FDA) obtained from DFF; p-xylylenediamine from terephthalaldehyde; m-xylylenediamine from isophthalaldehyde and bis (5-amino-2-furfuryl) ether from bis (5-formyl-2-furfuryl) ether.
  • FDA 5-bis (aminomethyl) furan
  • DFF-converted FDA is of particular interest, since FDA is a frequently used starting material in polyamine, polyamide and polyurethane syntheses, while DFF is widely available from biomass-derived resources.
  • the aromatic diamine obtained from the amination reaction can be purified to a high purity by the usual purification procedure comprising distilling off ammonia and any present solvent from the reaction mixture from which the hydrogenation catalyst has been separated and subjecting the residue to distillation or recrystallization.
  • Example 1 of US6696609 was reproduced in this Comparative Example, with identical experimental conditions to supress the generation of primary amine in the reaction system.
  • a 100 ml Parr reactor equipped with a mechanical stirrer was charged with 25 ml of methanol and 150 mg of Raney nickel. After being flushed for three times with nitrogen, the autoclave was then charged with 2 g of ammonia and, while a hydrogen partial pressure of 3 MPa was applied, heated to a temperature of 140°C. Thereafter, a methanolic solution obtained by dissolving 620 mg (5 mmol) of DFF in 25 ml of methanol was fed through a high-pressure metering pump to the autoclave over 1 hour. After completion of the feeding, the reaction mixture was stirred for another 1 hour at 140°C. Massive charcoal-like precipitate was observed to form in the reactor and the GC-MS analysis of the residual solution showed that no aminated product was formed.
  • Example 1 The operation of Example 1 was repeated in the absence n-butylamine, there was obtained only 18 mg of FDA, corresponding to a yield of 7%based upon the DFF used.
  • Example 1 The operation of Example 1 was repeated, expect that 0.4 mmol n-butylamine was introduced into the mixture of Raney Co and DFF. There was obtained 63 mg of FDA, corresponding to a yield of 25%based upon the DFF used.
  • Example 1 The operation of Example 1 was repeated, expect that 2.0 mmol n-butylamine was introduced into the mixture of Raney Co and DFF. There was obtained 96 mg of FDA, corresponding to a yield of 38%based upon the DFF used.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)
PCT/CN2015/083535 2014-07-10 2015-07-08 Process for producing aromatic primary diamines WO2016004867A1 (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
CN201580037775.9A CN106488905B (zh) 2014-07-10 2015-07-08 生产芳香族伯二胺的方法
CN201911137833.1A CN111116528B (zh) 2014-07-10 2015-07-08 生产芳香族伯二胺的方法
BR112017000203-5A BR112017000203B1 (pt) 2014-07-10 2015-07-08 processo para a produção de uma amina primária aromática
EP15819072.8A EP3166921B1 (en) 2014-07-10 2015-07-08 Process for producing aromatic primary diamines
EP20157956.2A EP3674285B1 (en) 2014-07-10 2015-07-08 Process for producing m-xylylenediamine
KR1020177002283A KR20170027792A (ko) 2014-07-10 2015-07-08 방향족 1급 디아민의 제조 방법
US15/324,932 US10899726B2 (en) 2014-07-10 2015-07-08 Process for producing aromatic primary diamines
JP2017500926A JP6704896B2 (ja) 2014-07-10 2015-07-08 芳香族第一級ジアミンの製造方法
US16/781,356 US11066377B2 (en) 2014-07-10 2020-02-04 Process for producing aromatic primary diamines

Applications Claiming Priority (2)

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CNPCT/CN2014/081945 2014-07-10
CN2014081945 2014-07-10

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US16/781,356 Continuation US11066377B2 (en) 2014-07-10 2020-02-04 Process for producing aromatic primary diamines

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US (2) US10899726B2 (enrdf_load_stackoverflow)
EP (2) EP3674285B1 (enrdf_load_stackoverflow)
JP (1) JP6704896B2 (enrdf_load_stackoverflow)
KR (1) KR20170027792A (enrdf_load_stackoverflow)
CN (2) CN106488905B (enrdf_load_stackoverflow)
BR (1) BR112017000203B1 (enrdf_load_stackoverflow)
WO (1) WO2016004867A1 (enrdf_load_stackoverflow)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017169739A1 (ja) * 2016-03-29 2017-10-05 株式会社日本触媒 複素環を有するジアミン化合物の製造方法
WO2018086491A1 (en) * 2016-11-09 2018-05-17 Rhodia Operations Process for production of aromatic compounds comprising at least two amine functions
JPWO2019017468A1 (ja) * 2017-07-21 2020-07-27 三菱瓦斯化学株式会社 ２，５−ビス（アミノメチル）フランの製造方法
US11396498B2 (en) 2017-10-11 2022-07-26 Mitsubishi Gas Chemical Company, Inc. Method for producing 2,5-bis(aminomethyl)tetrahydrofuran

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WO2019073988A1 (ja) * 2017-10-11 2019-04-18 三菱瓦斯化学株式会社 ２，５－ビス（アミノメチル）テトラヒドロフランの製造方法
CN111097421A (zh) * 2018-10-29 2020-05-05 中国科学院大连化学物理研究所 负载型金属催化剂及其催化醛类化合物制备伯胺的方法
CN114602461B (zh) * 2020-12-09 2023-04-07 中国科学院大连化学物理研究所 一种催化二元醛制备二元胺的方法
CN117229239A (zh) * 2023-08-10 2023-12-15 中科国生(丽水)新材料科技有限公司 一种2,5-呋喃二甲胺的制备方法
CN117645587A (zh) * 2023-11-28 2024-03-05 中科国生(杭州)科技有限公司 一种2,5-呋喃二甲胺的制备方法

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US20100222611A1 (en) * 2005-06-30 2010-09-02 Michael Leo Tulchinsky Process for the Reductive Amination of Aldehydes and Ketones Via the Formation of Macrocyclic Polyimine Intermediates

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US20100222611A1 (en) * 2005-06-30 2010-09-02 Michael Leo Tulchinsky Process for the Reductive Amination of Aldehydes and Ketones Via the Formation of Macrocyclic Polyimine Intermediates

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017169739A1 (ja) * 2016-03-29 2017-10-05 株式会社日本触媒 複素環を有するジアミン化合物の製造方法
JPWO2017169739A1 (ja) * 2016-03-29 2018-09-06 株式会社日本触媒 複素環を有するジアミン化合物の製造方法
WO2018086491A1 (en) * 2016-11-09 2018-05-17 Rhodia Operations Process for production of aromatic compounds comprising at least two amine functions
US10662142B2 (en) 2016-11-09 2020-05-26 Rhodia Operations Process for production of aromatic compounds comprising at least two amine functions
JPWO2019017468A1 (ja) * 2017-07-21 2020-07-27 三菱瓦斯化学株式会社 ２，５−ビス（アミノメチル）フランの製造方法
JP7173009B2 (ja) 2017-07-21 2022-11-16 三菱瓦斯化学株式会社 ２，５－ビス（アミノメチル）フランの製造方法
US11396498B2 (en) 2017-10-11 2022-07-26 Mitsubishi Gas Chemical Company, Inc. Method for producing 2,5-bis(aminomethyl)tetrahydrofuran

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EP3166921A1 (en) 2017-05-17
JP2017521430A (ja) 2017-08-03
US20200172501A1 (en) 2020-06-04
EP3166921B1 (en) 2020-02-19
CN106488905B (zh) 2019-12-17
CN106488905A (zh) 2017-03-08
US20170217916A1 (en) 2017-08-03
US11066377B2 (en) 2021-07-20
KR20170027792A (ko) 2017-03-10
CN111116528B (zh) 2023-08-01
BR112017000203A2 (pt) 2018-01-16
US10899726B2 (en) 2021-01-26
JP6704896B2 (ja) 2020-06-03
EP3674285B1 (en) 2022-04-06
BR112017000203B1 (pt) 2020-12-08
EP3674285A1 (en) 2020-07-01
CN111116528A (zh) 2020-05-08

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